JP2012530119A5 - - Google Patents
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- Publication number
- JP2012530119A5 JP2012530119A5 JP2012515554A JP2012515554A JP2012530119A5 JP 2012530119 A5 JP2012530119 A5 JP 2012530119A5 JP 2012515554 A JP2012515554 A JP 2012515554A JP 2012515554 A JP2012515554 A JP 2012515554A JP 2012530119 A5 JP2012530119 A5 JP 2012530119A5
- Authority
- JP
- Japan
- Prior art keywords
- polypeptide
- group
- fluorosialic
- glycosylated
- sugar acceptor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 23
- 108090000765 processed proteins & peptides Proteins 0.000 claims 18
- 229920001184 polypeptide Polymers 0.000 claims 17
- 102000004196 processed proteins & peptides Human genes 0.000 claims 17
- ZQJAHJWWLQMSQT-GEFQIMLOSA-N 3-fluorosialic acid Chemical class CC(=O)N[C@H]1[C@H](O)[C@@H](F)[C@H](C(O)=O)O[C@H]1[C@H](O)[C@@H](O)CO ZQJAHJWWLQMSQT-GEFQIMLOSA-N 0.000 claims 13
- -1 3-fluorosialic acid compound Chemical class 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 230000013595 glycosylation Effects 0.000 claims 10
- 238000006206 glycosylation reaction Methods 0.000 claims 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 8
- 125000003147 glycosyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 230000001225 therapeutic effect Effects 0.000 claims 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims 4
- 125000000837 carbohydrate group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000004001 thioalkyl group Chemical group 0.000 claims 4
- 108090000790 Enzymes Proteins 0.000 claims 3
- 102000004190 Enzymes Human genes 0.000 claims 3
- 108010006232 Neuraminidase Proteins 0.000 claims 3
- 102000005348 Neuraminidase Human genes 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000004820 halides Chemical class 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- ZQISRDCJNBUVMM-UHFFFAOYSA-N L-Histidinol Natural products OCC(N)CC1=CN=CN1 ZQISRDCJNBUVMM-UHFFFAOYSA-N 0.000 claims 2
- ZQISRDCJNBUVMM-YFKPBYRVSA-N L-histidinol Chemical compound OC[C@@H](N)CC1=CNC=N1 ZQISRDCJNBUVMM-YFKPBYRVSA-N 0.000 claims 2
- 102000003838 Sialyltransferases Human genes 0.000 claims 2
- 108090000141 Sialyltransferases Proteins 0.000 claims 2
- 125000000539 amino acid group Chemical group 0.000 claims 2
- 230000004071 biological effect Effects 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000012634 fragment Substances 0.000 claims 2
- 150000004676 glycans Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- 150000002772 monosaccharides Chemical class 0.000 claims 2
- 229920001542 oligosaccharide Polymers 0.000 claims 2
- 150000002482 oligosaccharides Chemical class 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229920001282 polysaccharide Polymers 0.000 claims 2
- 239000005017 polysaccharide Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 238000006276 transfer reaction Methods 0.000 claims 2
- LYLDIIUFTYRPPK-UHFFFAOYSA-N 1h-imidazole-2-sulfonic acid Chemical compound OS(=O)(=O)C1=NC=CN1 LYLDIIUFTYRPPK-UHFFFAOYSA-N 0.000 claims 1
- 102000015081 Blood Coagulation Factors Human genes 0.000 claims 1
- 108010039209 Blood Coagulation Factors Proteins 0.000 claims 1
- 102000019034 Chemokines Human genes 0.000 claims 1
- 108010012236 Chemokines Proteins 0.000 claims 1
- 102000007644 Colony-Stimulating Factors Human genes 0.000 claims 1
- 108010071942 Colony-Stimulating Factors Proteins 0.000 claims 1
- 102000004127 Cytokines Human genes 0.000 claims 1
- 108090000695 Cytokines Proteins 0.000 claims 1
- 102000003951 Erythropoietin Human genes 0.000 claims 1
- 108090000394 Erythropoietin Proteins 0.000 claims 1
- 108010051696 Growth Hormone Proteins 0.000 claims 1
- 102000018997 Growth Hormone Human genes 0.000 claims 1
- 108090001061 Insulin Proteins 0.000 claims 1
- 102000004877 Insulin Human genes 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- 102000015696 Interleukins Human genes 0.000 claims 1
- 108010063738 Interleukins Proteins 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 claims 1
- 239000003114 blood coagulation factor Substances 0.000 claims 1
- 229940019700 blood coagulation factors Drugs 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000021615 conjugation Effects 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002255 enzymatic effect Effects 0.000 claims 1
- 230000007071 enzymatic hydrolysis Effects 0.000 claims 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 claims 1
- 229940105423 erythropoietin Drugs 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- 230000001279 glycosylating effect Effects 0.000 claims 1
- 239000000122 growth hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 230000001900 immune effect Effects 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 229940125396 insulin Drugs 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000033885 plasminogen activation Effects 0.000 claims 1
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical group [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 claims 1
- 230000001850 reproductive effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims 1
- 108010004486 trans-sialidase Proteins 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
- OQFDABBAAQUYFY-UHFFFAOYSA-N trifluoromethyl phenylmethanesulfonate Chemical compound FC(F)(F)OS(=O)(=O)CC1=CC=CC=C1 OQFDABBAAQUYFY-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18743409P | 2009-06-16 | 2009-06-16 | |
| US61/187,434 | 2009-06-16 | ||
| PCT/GB2010/001188 WO2010146362A2 (en) | 2009-06-16 | 2010-06-16 | Materials and methods relating to glycosylation |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015121185A Division JP2015187153A (ja) | 2009-06-16 | 2015-06-16 | グリコシル化に関連する物質および方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012530119A JP2012530119A (ja) | 2012-11-29 |
| JP2012530119A5 true JP2012530119A5 (enExample) | 2013-08-01 |
| JP6091892B2 JP6091892B2 (ja) | 2017-03-08 |
Family
ID=43086298
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012515554A Active JP6091892B2 (ja) | 2009-06-16 | 2010-06-16 | グリコシル化に関連する物質および方法 |
| JP2015121185A Pending JP2015187153A (ja) | 2009-06-16 | 2015-06-16 | グリコシル化に関連する物質および方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015121185A Pending JP2015187153A (ja) | 2009-06-16 | 2015-06-16 | グリコシル化に関連する物質および方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9452223B2 (enExample) |
| EP (1) | EP2442831B9 (enExample) |
| JP (2) | JP6091892B2 (enExample) |
| CN (1) | CN102481377B (enExample) |
| CA (1) | CA2768155C (enExample) |
| ES (1) | ES2560557T3 (enExample) |
| PL (1) | PL2442831T3 (enExample) |
| WO (1) | WO2010146362A2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2768155C (en) * | 2009-06-16 | 2016-08-23 | The University Of Bath | Materials and methods relating to glycosylation |
| TW201442721A (zh) * | 2013-01-23 | 2014-11-16 | Daiichi Sankyo Co Ltd | 糖鏈修飾心房利尿鈉肽 |
| JP6562942B2 (ja) * | 2014-03-27 | 2019-08-28 | アカデミア シニカＡｃａｄｅｍｉａ Ｓｉｎｉｃａ | 反応性標識化合物およびその使用 |
| RU2656140C2 (ru) * | 2016-11-14 | 2018-05-31 | Федеральное государственное бюджетное учреждение "Государственный научный центр Институт иммунологии" Федерального медико-биологического агентства России | Способ получения гибридного белка, состоящего из рекомбинантного белка аналога интерферона гамма, конъюгированного с олигосахаридом |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992016640A1 (en) | 1991-03-18 | 1992-10-01 | The Scripps Research Institute | Oligosaccharide enzyme substrates and inhibitors: methods and compositions |
| US5770407A (en) * | 1996-12-10 | 1998-06-23 | The Scripps Research Institute | Process for preparing nucleotide inhibitors of glycosyltransferases |
| ES2411007T3 (es) * | 2001-10-10 | 2013-07-04 | Novo Nordisk A/S | Remodelación y glicoconjugación de péptidos |
| US7226903B2 (en) | 2001-10-10 | 2007-06-05 | Neose Technologies, Inc. | Interferon beta: remodeling and glycoconjugation of interferon beta |
| CA2500653A1 (en) * | 2002-10-16 | 2004-04-29 | The Scripps Research Institute | Glycoprotein synthesis |
| JP2010523582A (ja) | 2007-04-03 | 2010-07-15 | バイオジェネリクス アクチェンゲゼルシャフト | グリコｐｅｇ化ｇ−ｃｓｆを用いた治療方法 |
| JP2011503101A (ja) | 2007-11-09 | 2011-01-27 | バクスター・インターナショナル・インコーポレイテッド | 修飾された組換え第ｖｉｉｉ因子およびフォンウィルブランド因子ならびにその使用方法 |
| CA2768155C (en) * | 2009-06-16 | 2016-08-23 | The University Of Bath | Materials and methods relating to glycosylation |
-
2010
- 2010-06-16 CA CA2768155A patent/CA2768155C/en active Active
- 2010-06-16 PL PL10727485T patent/PL2442831T3/pl unknown
- 2010-06-16 US US13/378,192 patent/US9452223B2/en active Active
- 2010-06-16 JP JP2012515554A patent/JP6091892B2/ja active Active
- 2010-06-16 ES ES10727485.4T patent/ES2560557T3/es active Active
- 2010-06-16 EP EP10727485.4A patent/EP2442831B9/en active Active
- 2010-06-16 WO PCT/GB2010/001188 patent/WO2010146362A2/en not_active Ceased
- 2010-06-16 CN CN201080031987.3A patent/CN102481377B/zh active Active
-
2015
- 2015-06-16 JP JP2015121185A patent/JP2015187153A/ja active Pending
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